


The Mess You've Made of Me

by EmberSparks



Category: Supernatural
Genre: AU, Alternative Univese, Anal Sex, Colonial era, Fingering, Fluffy Smut, Hand Jobs, Healing Sex, Hooker, Hooker!Cas, M/M, PWP, Past Sexual Abuse, Pirates, Plot What Plot, Porn Without Plot, Prep, Pro!Cas, Prostitute, Sailing, Sam Winchester - Freeform, Sastiel - Freeform, Sex, Sex Work, Smut, Supernatural - Freeform, Whore!Cas, brothel, castiel - Freeform, colonial fic, hints of bdsm, past Destiel, past abuction, plotty porn, whore, whores
Language: English
Status: Completed
Published: 2015-11-29
Updated: 2015-11-29
Packaged: 2018-05-03 22:08:38
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,171
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5308814
Author URL: https://archiveofourown.org/users/EmberSparks/pseuds/EmberSparks
Summary: <blockquote class="userstuff">
              <p>Castiel is used to this life. To the long nights with strange men, to the sailors cursing and drinking in his Master's house. What he isn't used to is kindness. Goodness. Or the sweet looking Sam that comes offering his own medicine to the seasoned whore...which of course, Castiel will delight in corrupting. Or will he?</p>
            </blockquote>





	The Mess You've Made of Me

Castiel could still hear their ruckus laughter echoing up from the floors below. The little oil lamp on his nightstand flickered, and even bounced on the battered wooden surface. The shaking and quaking was fine….But the noise! The grunts and moans from all the rooms around his. At least Castiel was done for the night.

                They’d fucked with reckless abandon.

He fed the grapes and plied them with sweet wines and old ales. Been grabbed and shoved and held for hours it seemed. Now Castiel lay on his stomach, his sweat and that of others drying on his skin, not even enough energy to clean himself before bed. The wash basin was left untouched, and it was likely the only thing.

He gazed out his window, looking at the stars above the port city, thinking there had not been so tumultuous a night since pirates, more savage than even these sailors, had taken him from his home. To this house whose rooms were many and guests paid for the pleasure of visiting, but never staying. Walls that had seen every sort of sin…and floors that creaked before the threshold of his door.

But, Castiel thought, he was done for the night.

                 
                “This is a private room” he said, without even lifting his head. What difference would it make? He didn’t have the energy for a prolonged protest.

                “I’m not…looking for anything”

                Castiel felt his brow furrow, before he summoned the will to look up. That timid a voice was ill fit for a sailor’s life. That gentle tone would command no barter or trade, nor fend off any nefarious sea fairer. In fact Castiel did not recognize it at all. The sight of the boy was completely unfamiliar to him.

                Boy was hardly the proper word.  The youth had to stoop to enter his door way; his tanned skin and his obvious strength showed that yes he had been in the sun and at the sea. Castiel was familiar with the rough bodies of the sailors….still the one before him was softer somehow. Maybe it was just that childlike face.

                “I thought you could use some” he murmured, offering a little jar of something that smelled strong, and herby.

                Castiel’s confusion only increased.

                But he was not used to such kindness, nor such an innocent offer. Something Castiel was not used to hearing…something he did not entirely trust.  Old habits do die hard.  He turned his head away with a haughty jerk of his chin, not bothering to cover his nakedness or to attempt to flee.

                “Another pill or potion? I assure you no drug is needed to have your way with me” Castiel huffed, and rested his head back on his pillow, and pointedly ignored the boy.

                “It’s not a sedative. Or a pill.” The boy protested in earnest, moving further into the room. The door swung nearly closed behind him. “It’s a salve, for bruises and aching muscles.”

                Castiel made no move to acknowledge him. He could feel the tingle across the bare skin of his back, the familiar sensation of being eyed up and down. It was a constant here. He could almost hear the boy hesitate, pause to lick his lips.

                “I’ll show you”

                Oh Castiel knew those words well. He opened a bright blue eye, wondering if he would see the youth’s shadow looming over him- but the shadow shrank away. The whore leaned up on his elbows, peering over the side of his bed to see the sailor sitting at the edge. Beyond confusing now. He was actually on the floor, though with his height Castiel was practically at eye level.

“It takes away the pain, lessens the swelling too” The boy’s long fingers unscrewed the lid of his jar and a much sweeter smell was in the air. He took a dab, and spread it on his split knuckles.

Castiel groaned softly. The master of the house, Castiel’s master, would have his head if he knew a guest was sitting on the floor next to his bed. He could not have that.

“I do see…” the whore smirked, a thought flickering in his mind. There was that urge. He’d seen it before with others. The desire to taint. To stain something that was pure….it was overwhelming.

“And will you administer it then? Do you know where I ache?” he raised his hips, moonlight falling across his pale ass, bruised from many hands of many men tonight.

He smirked at the new pink color in the boy’s cheeks.

“I can…guess” the boy said, coughing a bit to clear his throat. How quaint. “They were very unkind to you”

Castiel blinked.

There was an honest concern in the youth’s voice, and the way he tipped his head back, kind eyes staying easily on the whore’s face.

That was disarming.

So much so, that Castiel did not even have his wits about him enough to flinch when a hand came towards his face. The fingers were long, and the palm was calloused. But when he touched Castiel, it was so tentative, brushing some of his dark hair away. The boy still blushed.

“I heard, that your name is…Castiel?”

Castiel nodded, watching the boy start to turn from pink to red before his eyes.  He ducked his head, back to his little jar of slightly green clear ointment, painting it over those rough fingers.

“My name is Sam….May I?”

                Castiel had managed to regain himself. He shrugged his shoulders all too casually, and slipped his arms back under the cool silk of his pillows.

“You may….but only if you’ll join me, Sam?” his voice was a purr, caressing the boy’s name as he gestured invitingly to his bed.  He waited until he felt the dip of another person’s weight before adding

“And you may even call me Cas….or whatever you will, as any other man will do on any given night. Especially as rambunctious a celebration as this. One of them even called me Angel”

“That would be my brother” Sam rolled his eyes. “And his crew have been on the open sea for the past year….Apparently they, had some built up frustration”

Castiel could have laughed at the awkwardness of those words. He thought he was more professional than that. But it did not matter. Because Sam’s palm, slick with ointment, had begun working at Castiel’s….shoulders.

The boy’s long fingers were deftly massaging the tingling substance into the whore’s muscles, making him sigh ever so softly. He simply had not realized he was hurting so. Until it ceased. Castiel peeked up a bright blue eye.

“Brother? The Captain with short hair and a filthy mouth… I am certain I serviced him tonight” he smirked “Does that not disgust you?”  He looked over his shoulder, seeking a rise from the boy. To be reviled the way he reviled himself. “And are you claiming not to be in need of that release?”

Sam was rubbing his salve covered hands together, a mess Castiel did not relish despite how it soothed.

“Yes, that’s my brother Dean” he snorted. Sam was more focusing on rubbing his way down over Castiel’s spine, his sides, visibly easing the tension from his body despite his mouth. It seemed then the rest of the whore’s words seemed to sink in. Even as Castiel sighed and sank further into his plush bedding.

“You don’t disgust me Castiel. You have been used so much, and I know you hurt so, I am not disgusted by you….and, I can handle my own release, thank you”

The boy was bright red again.

                Castiel chuckled softly. The Captain had been rather entertaining. Creative, one might say, with Castiel and a few of his house mates. The whore might have enjoyed himself if that had been his only “fun” that night.

                He looked over at Sam, a patronizing pout on his lips.

                “I assure you, you are not nearly as skilled about bringing your release as I am”

                 “Dean is a goodhearted man” Sam huffed, blowing his long hair from over his face. Castiel continued to gaze steadily at him, waiting for the answer to the rest of his words. Sam shifted on his knees, his kneading motions now at the small of the whore’s back.

                “Yes, Castiel, I’m sure you are. But you have had a rough night….and I don’t want you to hurt any more than you already do” he said firmly, hands sliding down farther.

                Castiel opened his mouth to protest at once. But, then again, Sam’s hands were finally where he wanted them. So he arched his back sweetly. The way his guests often liked.

                “You are….certainly not hurting me now” Castiel murmured, with a light tone of surprise.

                He paused for a long moment, letting the boy continue to ease him with the salve, massaging those lovely fingers into the flesh of his ass. The soreness was leaving him rather quickly. Yet, what Castiel still expected was not happening. He expected prodding at least. For the boy to show some eagerness towards his entrance, still raw with all the friction tonight. Or perhaps a nudge to his private bits. Which Castiel had to admit even to himself were woefully under used in his line of work.

                Alas, nothing.

                The sailor’s hands moved along the backs and outsides of his thighs chastely….unbelievably chaste for the situation they were in! Castiel huffed into his pillow. His body was tingling from the salve and the attention and it did not appear those aches would be eased any time soon. Not of their own accord.

                “Sam, sweetheart, you have been so good to me” Castiel simpered. “Won’t you at least let me be good to you?”

                He heard a sharp inhale of breath, and saw the boy lick his lips.

                “I….you don’t deserve to be hurt like this” Sam murmured, ducking his head down as he spread Castiel’s cheeks apart. His hole was irritated and puffy. And he fought not to hiss in relief when the cool ointment was applied.

                “And, I don’t want you to think, that I’d ever want that”

                Castiel turned his head back to face forward, keenly aware of Sam’s weight behind him. He spread his legs a bit wider. Giving more access. Moaning softly as the burning sensation eased. Magical salve….which, of course, gave Castiel an idea.

                “And…if it weren’t to hurt me?” he asked the headboard of his old, battered bed.

 He was having trouble looking directly at the boy. He could feel his gut start to twist with guilt at his own manipulations. Cas could hardly take such kindness. The only thing he could think to ease it, was to do what he did best.

“If…..I need this salve, deeper inside me…to soothe me of course” he asked, flexing against the tip of the slick finger.

He heard Sam hesitate.  Perhaps the boy was not as naïve as the whore expected. He certainly was comfortable enough with a naked man, more so than some men with wives and children had been. Surely, this sweet young man would not foil a whore’s plan?

“If….”

Castiel held his breath.

“…if it wasn’t to hurt you….then yes, I could give you what you want” Sam finally decided.

Castiel hid his smirk of victory in his pillow.  He nodded, only to gasp when one of those blessedly long, slick fingers slid inside him.

“Oh…it does not hurt, far from it my sweet Sam” Castiel praised. He looked back over his shoulder, his blue eyes wide in what he hoped was an innocent look. Though it felt like a particularly poor attempt when looking at the sailor.

“It feels so good,” he purred, flexing again, his voice catching to add to the effect….playing it up a bit…but the salve did feel pretty good after the night he had. But Castiel whined aloud when the digit suddenly stopped.

“Come on now Cas, I’m not dim” Sam said, an audible scowl on his lips. The whore made a sound of protest, loudly, lifting his hips and bucking back towards the hand.

“I was not pretending, per say…” Castiel pouted over his shoulder again. “Alright…perhaps exaggerating slightly” he huffed a breath and returned his chin to his pillow.  But it seemed his sweet boy was serious. He was not taking kindly to being toyed with. So Castiel lowered his voice.

“You won’t leave me wanting, will you?” Castiel asked, shifting his weight slightly onto his knees, lifting his hips to display his poor cock, already starting to hang hard between his thighs. “As so many have tonight?”

He felt Sam’s resolve soften to him again.

“Of course not”

He eased a second finger into Cas, who moaned gratefully. He resisted the urge to buck wildly again. Sam twisted and scissored him open. Really Castiel did not need so much gentleness. But the way those fingers, those long fingers he was sure he’d adore the rest of his days, massaged his little bundle of nerves was to die for. All with that tingling salve.

Castiel gasped again; preparation was never this good for the whore. He often had to rush to do it himself before he was put to work for the night….or he was left at the mercy of a guest’s clumsy attempts. This…was so very nice.

“Now Sam, do not injure my pride….won’t you let me please you in turn?”

“Is that what you really want Cas?”

“Yes, yes I want to so much” Castiel said vehemently.

The boy hesitated again. But then, he nodded. Cas clutched the bed sheets as he felt Sam shift above him, moving over him properly, anticipation building in the  blue eyed man’s gut.

And then a kiss landed against his temple.

And Castiel felt a different heat build beneath his skin, reddening his face.

Sam continued his gentle ministrations. Making sure the salve eased the worst of the soreness of Castiel’s inner walls, taking his time to make sure….Cas, was comfortable. Castiel arched up again. He nuzzled Sam’s jaw, little needy pants escaping his lips.

He was relaxed yet so tightly wound. It was so nice. Nice to have someone giving him so much attention without demanding it from him. The gentle way Sam just turned his head, pressed their lips together firmly, the way he felt the heat of Sam pressed against every inch of himself.

“You may have, whatever you wish” Sam whispered hotly.

Castiel made a breathless sound. He felt the stretch of a forth finger, the next nudge to his sweet spot leaving him mewling with pleasure.  He moaned against Sam’s lips, genuine and unabashed this time.

As much as he loved the stretch of all those digits, Castiel simply could not help the condescending little raise of his eyebrow. Men Sam’s size were not necessarily proportional in that sense. But the youth just chuckled and pulled back. Cas rather regretted that.

He rolled onto his back finally, leaning up on his elbows to watch Sam curiously. Watch him disrobe almost clumsily in his haste, yet he had the other’s rapt attention. Cas was almost shocked. He expected his sweet boy to be so clean and pure.  What he saw were scars. A myriad of scars across curves of muscles, sun kissed skin interrupted by white or red scar tissue.

Castiel had been taught not to stare. To take the feeling from the physical act, by not focusing too much on who he was partnered with. But Sam seemed to defy….everything Castiel knew really.

                “Now, aren’t you incredible” Cas praised softly. 

His face split into a much wider smile when his eyes finally found their way down to Sam’s…impressive cock. Castiel felt his own length start to drip eagerly. 

                Castiel leaned back, pulling himself up with the headboard. His legs spread eagerly and fixing Sam with the very best come hither look he could manage.

                “Am I?” Sam laughed softly, leaning forward toward the bed.

                “You are”  Castiel purred in turn, watching eagerly as the boy crawled over him, his arms going around those broad shoulders.

                Cas was nearly vibrating in his skin. He was not at all used to having to wait so very long, or being filled with so much anticipation. Sam’s kisses were wilder now. But still sweet without the taste of ales or beers.

                Castiel gave a soft cry when he felt a calloused hand around him. The salve’s tingling effect was magnified by the hand on his cock; which he had to look down in disbelief at. No one touched him like that.

                “Sam…!” 

And this time he was not playing. He was simply overwhelmed, his arms falling back against the bed as the boy rubbed the pad of his thumb along his sensitive head, spreading the white that collected there.

                “I want you to come for me Cas” Sam murmured against his neck, nipping at his skin and sucking lightly.

                 “N-Now?” he gaped, utterly disarmed by this man he had not even wanted in his room before.

                “Yes” Sam nodded, licking his lips as he did, panting against Castiel’s. He could tell waiting was killing Sam. But still he insisted. “I’ll make you come again, don’t you worry. But I want you…to have this one” he insisted eagerly.

                Castiel was already arching his back off the bed, bucking up to Sam’s hold. He was not worried about more. He just….it was…too much.

                “I can’t I can’t!” Castiel shook his head violently back and forth. Everything in him was rebelling against it, every experience. He was never to come before a house guest. Never ever.

                But Sam insisted.

“Yes, yes you can” he sped his movements, gripping harder, humming against Castiel’s chest, his hand more insistent. “You want to give me what I want right?”  His tongue dragged over one of Cas’s nipples, driving him crazier still. “I want you to come for me”

                Castiel cried out again. He could not bring himself to answer Sam with words.  His body lurched forward, spilling hotly over the long fingers and knocking him breathless. He could feel Sam surrounding him. Overwhelmed. Completely overwhelmed.

                Sam still eased him through his bliss.  Giving him long strokes, prolonging his pleasure as long as he could, longer than Castiel thought possible. Then again, his particular brand of skills had never been used on him.

                “That…” Cas panted “was not nice”

                “I look a lot nicer than I am” Sam smirked, licking the streaks of white from his fingers. Slowly, all while keeping his darkened eyes on Castiel’s.

                His spent cock throbbed hard, his tired body fluttering. Castiel felt boneless, all the tension gone from him, lax in his bed while still tangled up with the handsome sailor. He had to concentrate….but Cas managed to wrap his arms back around Sam’s shoulders.

                “Is that so?” Castiel chuckled hoarsely, leaning up to nuzzling Sam’s jaw. “Won’t you be nice enough…to give me what you promised?”

                Sam groaned loudly. Castiel was reaching for the man’s thick cock, but his hand was batted away, in favor of Sam slicking himself with salve. He bit back another sound. A sweet one that had Cas’s thighs going around his waist as they both hurried to align.

                “Fuck”

                Castiel was not sure which one of them said it, their breaths tangling together as Sam pressed to his entrance. He moved so smooth and slow.  Cas barely had to flex to…but damn, he was big. His hands moved to the scar covered shoulders, gripping to them, and their lips sloppily in their movements now.

                “A-are you alright Cas?” Sam was trembling, fighting to keep still, waiting for Castiel to nod. Which he did. Enthusastically.

                “Darling, I am far better than I have been in a long- ugh do that again please” Cas demanded, his body rocking the moment Sam moved, demanding he thrust back harder. 

                “Of course love, of course” the ma n obliged.

                Cas’s spent cock was thickening quickly against his stomach.

                He gripped Sam wherever he could, his legs around the man’s waist, his fingers scrabbling along his back for purchase. Cas endeavored to meet his movements but he was utterly exhausted from it all. The salve was as good inside him as it was outside, and if felt even better with Sam’s thick cock. Castiel was finally being stretched in just the right way. 

                He could feel the way Sam throbbed as he moved, rocking into him still.  Castiel was panting already….when there was a hand back on his cock.

                “I’m close” Sam growled softly, rocking the rickety bedframe loudly with every move.  “I want you…to come again, Angel…can you do that for me?”

                Castiel made a garbled, high sound. How was he so articulate right now?

                “F-fill me up Sam, please, I need to feel it” Cas begged.

                He was coming undone, he knew it. Sam would have his way either way, especially the way he tugged on his oh so sensitive cock.

                Sam did not need much convincing it seemed. He gave a throaty grunt, his hips jerking and rolling as Castiel felt his insides grow warm and hot and wet.

                He was done for.

                Castiel arched up until he collided with Sam, hardly conscious for the flurry of bliss, their lovemaking consuming them like gentle fire. Until all that was left was a pile of lank limbs, and the stickiness Cas could feel on his belly.

                They were still panting.

                Castiel stared blearily up at his ceiling, wondering how in the hell he could ever work again. How could he take another sour night when he’d known this sweetness? This goodness?

                “Oh, the mess you’ve made of me boy” Castiel murmured, kissing the top of Sam’s fluffy head.

                Sam, it seemed was attempting not to crush Castiel, pushing himself off the whore on his weak arms, turning them so Cas lay against his chest.

                “Are you alright love?” he asked, voice gentle, innocent as it ever had been.

                Castiel sighed against his skin, slick with sweat and salve, the world coming back around him. Like the chill creeping in from his open window.  He closed his eyes against it. For this had to be a dream. These soft touches and sweet lingering, not moving on to the next to bend over. Castiel refused to wake.

                “Just, stay with me, a moment longer” the whore begged, flexing around Sam’s softening cock.

                His long fingered hands were still there, his lips peppering kisses over Castiel’s face and neck. Rubbing his sore muscles. Nuzzling his dark hair.

                “I’m not going anywhere”

                And with that, Castiel was woken up.

                The real feelings came rushing back to his body. His skin was sticky, his body still bruised underneath it. 

                And he was still being fucked.

                “But you will though, you shall leave me, just as every other has” the dark haired whore muttered resentfully. He pushed himself free of Sam’s hold, standing, wobbling at the edge of the bed, before going to search for the wash basin.

                Sam let him pull away.  But the sadness showed in his young face.

                “Not if, if you didn’t want it that way” he licked his lips, pulling the blankets over his lap. He looked back up at the whore, tending to his tender bits with water. “I have money, we do, from our mother. Dean spent his on a ship. But I could use mine to free you”

                Castiel straightened up slowly. “And why would you do that for me Sam? What have I done to earn an honest man’s favor?” he asked softly with a sad, sarcastic little smirk over his shoulder.                

                Sam kept his gaze.

                “Something, something I can see in your eyes Cas,” the boy said, moving off the side of his bed. He chuckled though, a bitter sound. “That, and I know what it’s like to be a slave to someone’s whims” he admitted and Castiel felt himself drop the washing cloth he held.

                The boy offer his arm, pulling the bracelets he’d never take off aside. Showing the whore the burn mark on his skin.

                Pirate.

                Castiel froze in place, his mind reeling and his heart thumping up in his throat and ears. He should have known. Someone like Sam was too good to be true.  Sailors were bad enough in their own right, yet this criminal had been more decent to Cas than…..he’d been more than decent. He’d been loving.

                “I-I don’t deserve your kindness” the whore stammered, his eyes cast down.

                Sam was standing up, and Castiel felt his breath catch. But he did not flinch. And the long fingers caressing his cheek were gentle as ever. The boy had to lean down to kiss him. And Castiel had to lift himself up to respond.

                “It’s all up to you Cas, ”

 

**Author's Note:**

> based off of an rp with anonymous partner.


End file.
